Outsider
by RGLH2017GG
Summary: A take on Rory's life post AYITL


**A/N: This takes place after AYITL. It is from an outside perspective**

It's been ten years since my college graduation from Duke University and somehow I am back at Chilton for career day. I didn't know what to expect after being gone for so long from the Hartford scene but when I was asked to come speak to the students, I figured why not. I was still single and I'm sure some of my fellow classmates would be there who were still single. I took them up on their offer and decided to make sure I looked good before I went.

I was still a ladies man with no intention of settling down but working with my father at his law firm, he wanted to retire but he would not do so until I was married. I figured I had a couple more years until I had to settle down. As I pulled into the parking lot I saw two people I never expected to see again after 15 years, Paris Gellar and Rory Gilmore or Mary as I liked to call her in high school.

I had gotten sent to military school before Rory and I had a chance and I knew that she could have been the girl to change me but now 15 years later, I still believed that but I wasn't sure if I was willing to pursue her again.

I watched them go into Chilton before I got out of my car and did the same. I didn't see them when I walked in and figured they had gone into their classrooms for their presentations. I headed to do my presentation and get out of there quickly so I could mingle with some of the single ladies. All of the young girls in my class seemed to be entranced by me which always made my ego feel better. I finished my presentation pretty quickly so I left and went out into the hall. I spotted my ex-girlfriend, Summer, from high school so I approached her.

We started catching up and flirting. I couldn't believe how easy it was for girls to fall at my feet. She told me how she was divorced and living in Hartford. I knew she was just another trophy wife who was looking for her next Hartford husband, which would not be me. While we were talking, I spotted Rory and Paris walk into the main hall talking. I saw as Paris looked over at me and then at Rory before scurrying off to the bathroom. Rory followed and I wondered what they could be talking about. As I continued to make my way around the room, I saw them emerge from the bathroom and I figured now was my chance to see if there was still a spark between Rory and I.

I walked over to them and saw Paris panicking so I decided to have some fun. "Well, well, if it isn't Paris and Mary."

Paris and Rory simply glared at me before Rory responded by telling me that her name was Rory, not Mary.

I knew her name but it was always fun to see her get angry. I figured I would try and see what they were up to. "So what have you ladies been up to for the past fifteen years?"

Rory filled me in on her journalism while Paris simply said that she was a fertility specialist. Before I could continue the conversation, the headmaster came out and called us individually to speak with us about our careers and future work with Chilton.

I watched as Rory walked away again and knew that in the next few days while I was still in Hartford I would try and seek her out before returning to London.

* * *

My time in Hartford passed quickly and I never got to see Rory again. I was thrown into society events the few days I was there and didn't even get to catch up with old acquaintances before heading back home to London.

Days turned to weeks, which turned to months and before I knew 4 months had passed since the Chilton reunion. I couldn't stop thinking about how Rory definitely didn't look like a Mary anymore but at the same time she still maintained innocence with her look.

I had tried to find out more information about her but her Facebook page didn't offer much and neither did any of her other social media accounts. They were mainly focused on stars hollow or the stars hollow gazette. However, about a month ago her posts stopped and I haven't been able to see what she has been up to since then.

Today was a big day for me at work as we had won a big case that we had been working on. I decided to head to my favorite coffee shop after work, which was across from a park. I loved sitting there and doing work while looking out at the park. As I sat there today, my mind drifted on to how unfulfilled I felt at times with my life and as always my thoughts drifted back to the one girl that had ever turned me down.

I could picture the way she used to look at me during school and how she had looked at Chilton. Before I knew it, I saw her walking towards a bench in the park across from the coffee shop. I couldn't believe my luck. The one girl I had been thinking about nonstop was in my city. I sat there contemplating what I would do and say to her. I watched as she sat down alone on the bench and looked fidgety. She was facing the coffee shop but was looking anywhere but there. It seemed as though she was waiting for someone. Before I could wonder who, I saw a blonde man walk over to her. She stood up and he pulled her in for a hesitant hug.

I knew the blonde looked familiar but he couldn't figure it out. As I watched them, I saw them sit back down on the bench and could see that the blonde man had his eyebrows furrowed while Rory seemed to be rambling. All of a sudden I saw the man look shocked at something she had said and they both sat there looking at each other. I didn't know what had just happened but it gave me a moment to recognize the blond man. It was no other than the Logan Huntzberger. Infamous for his pranks and his reputation with the ladies, Logan was the man that most of Hartford's bachelors aspired to be. I knew I had aspired to be him at one point. His pranks were legendary and he always had a new woman even without trying.

I turned back to see Logan smiling at Rory and she was crying slightly but was also smiling. Before I knew it, Logan had pulled Rory into a passionate kiss in the middle of the park. I couldn't believe that Rory was seeing Logan, last I had heard he was engaged but had recently broken it off a few weeks ago. Rory had never even given me a chance but here she was with a man who was even more of a playboy than myself. I watched as Logan looked deeply at Rory and began talking. As he talked both of their smiles seemed to grow even larger. I felt like I was witnessing an intimate moment but I couldn't look away.

I watched as they moved closer together with his arm around her shoulders and she placed a hand on his thigh. Then before I could process what was happening, logan placed his other hand on Rory's stomach and before I knew it I realized that she was pregnant. Her small bump had become visible and I slowly put together the pieces. Rory and Logan must have been seeing each other while he was engaged and now she was pregnant with his child. I couldn't believe how much my Mary had changed. I suddenly felt like an outside witnessing a moment that I shouldn't have. I decided to leave the coffee shop through the back, hoping to avoid any more sightings of those two.

* * *

It had been a year before I returned to Hartford again for the annual Christmas gala which was being hosted by my mother this year. I had decided to attend solo as I didn't want to deal with a clingy date tonight. I had been there for an hour and I was extremely bored. As I was about to head out to find a subparty, I saw them come in. I couldn't believe my eyes, I felt as though they were playing tricks on me.

Rory walked in wearing a strapless wine color mermaid gown with a white bow tied around the waist, while logan just looked like always, perfectly put together. I couldn't take my eyes off of them and watched as they made there way over to her grandparents.

I knew I needed to get out of there fast. Before I could make it to the exit, my mother approached and took me to introduce me to some people. Before I knew it, she was taking me over to Logan and Rory.

"Tristan, I would like to introduce you to Logan and Rory Huntzberger." My mother said.

"Rory, nice to see you again. Logan, nice to meet you, I'm Tristan Dugrey." I introduced myself.

My mother seemed surprised but I simply explained that Rory and I had gone to Chilton together. Before I could get away my mother began pestering Rory and Logan with questions. However annoying it was, it was also informative.

Rory and Logan had gotten married about 8 months ago and had welcomed a baby boy six months ago. They were living in London but made frequent visits to Connecticut. I couldn't listen anymore, so I excused myself and hid for the rest of the evening.

I had seen their relationship from the outside. The moment they had shared and I knew from the way they looked at each other, their bond was unbreakable. I hoped to find that one-day and figured if Logan could do it, maybe I could. I knew it wouldn't be easy because there was no one like Rory but I would finally try to settle down.


End file.
